Asymmetric synthesis of (+)-(S,S)-reboxetine via a new (S)-2- (hydroxymethyl)morpholine preparation

Organic Letters

Volumn 7, Issue 5, 2005, Pages 937-939

  Brenner, Eric ^a   Baldwin, Ronald M ^a,c   Tamagnan, Gilles ^a,b  

^a YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Inst for Neurodegener Disorders   (United States)

^c VANDERBILT UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (HYDROXYMETHYL)MORPHOLINE; CHROMIUM; MORPHOLINE DERIVATIVE; REBOXETINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; OXIDATION; STEREOSPECIFICITY; SUBSTITUTION REACTION;

CATALYSIS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; MORPHOLINES; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 15044347050     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050059g     Document Type: Article

References (34)

1. (a) Hajos, M.; Fleishaker, J. C.; Filipiak-Reisner, J. K.; Brown, M. T.; Wong, E. H. F. CNS Drug Rev. 2004, 10, 23.
2. (b) Versiani, M.; Cassano, G.; Perugi, G.; Benedetti, A.; Mastalli, L.; Nardi, A.; Savino, M. J. Clin. Psychiatry 2002, 63, 31.
3. (c) Wong, E. H. F. et al. Biol. Psychiatry 2000, 47, 818.
4. Berzewski, H.; Van Moffaert, M.; Gagiano, C. A. Eur. Neuropsychopharmacol. 1997, 7, S37.
5. Wong, E. H. F.; Ahmed, S.; Marshall, R. C.; McArthur, R.; Taylor, D. P.; Birgerson, L.; Cetera, P. Patent WO 2001001973, 2001; Chem. Abstr. 2001, 134, 105849.
6. (a) Prabhakaran, J.; Majo, V. J.; Mann, J. J.; Kumar, J. S. D. Chirality 2004, 163, 168.
7. (b) Melloni, P.; Della Torre, A.; Lazzari, E.; Mazzini, G.; Meroni, M. Tetrahedron 1985, 41, 1393.
8. (c) Melloni, P.; Della Torre, A.; Carniel, G.; Rossi, A. Patent DE 3540093, 1986; Chem. Abstr. 1986, 105, 191107.
9. (d) Melloni, P.; Carniel, G.; Della Torre, A.; Bonsignori, A.; Buonamici, M.; Pozzi, O.; Ricciardi, S.; Rossi, A. C. Eur. J. Med. Chem. 1984, 19, 235.
10. Raggi, M. A.; Mandrioli, R.; Sabbioni, C.; Parenti, C.; Cannazza, G.; Fanali, S. Electrophoresis 2002, 23, 1870.
11. Ohman, D.; Norlander, B.; Peterson, C.; Bengtsson, F. J. Chromatogr. A 2002, 947, 247.
12. (a) Cases-Thomas, M. J.; Haughton, H. L.; Lamas-Peteira, C.; Ouwerkerk-Mahadevan, S.; Masters, J. J.; Simmonds, R. G.; Rudyk, H. C. E.; Walter, M. W. Patent WO 2004018441, 2004; Chem. Abstr. 2004, 140, 217649.
13. (b) Clark, B. P.; Gallagher, P. T.; Haughton, H. L. Patent WO 2004018440, 2004; Chem. Abstr. 2004, 140, 235726.
14. (c) Walter, M. W.; Clark, B. P.; Gallagher, P. T.; Haughton, H. L.; Rudyk, H. C. E. Patent WO 2004017977, 2004; Chem. Abstr. 2004, 140, 235724.
15. (a) Szczepankiewicz, B. G.; Heathcock, C. H. Tetrahedron 1997, 53, 8853.
16. (b) Iffland, D. C.; Davis, J. E. J. Org. Chem. 1977, 42, 4150.
17. (a) Berg, S.; Larsson, L.-G.; Renyi, L.; Ross, S. B.; Thorberg, S.-O.; Thorell-Svantesson, G. J. Med. Chem. 1998, 41, 1934.
18. (b) Ono, S.; Yamafuji, T.; Chaki, H.; Maekawa, M.; Todo, Y.; Narita, H. Patent EP 383281, 1990; Chem. Abstr. 1990, 114, 81222.
19. Mancuso, A. J.; Huang, S.; Swern, D. J. Org. Chem. 1978, 43, 2480.
20. Reed, P. E.; Katzenellenbogen, J. A. J. Org. Chem. 1991, 56, 2624.
21. Chrisman, W.; Singaram, B. Tetrahedron Lett. 1997, 38, 2053.
22. (a) Yamaguchi, M.; Takata, T.; Endo, T. J. Org. Chem. 1990, 55, 1490.
23. (b) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559.
24. Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029.
25. De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041.
26. Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Lin, T. M. H. Tetrahedron Lett. 1985, 26, 2951.
27. (a) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431.
28. (b) Hamashima, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 691.
29. (c) Loughhead, D. G.; Flippin, L. A.; Weikert, R. J. J. Org. Chem. 1999, 64, 3373.
30. Aggarwal, V. K.; De Vicente, J.; Bonnert, R. V. Org. Lett. 2001, 3, 2785.
31. (a) Wilhelm, R.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1 2000, 3808.
32. (b) Kamikawa, K.; Watanabe, T.; Daimon, A.; Uemura, M. Tetrahedron 2000, 56, 2325.
33. (c) Mahaffy, C. A. L. J. Organomet. Chem. 1984, 262, 33.
34. Mitsunobu, O. Synthesis 1981, 1.